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The benzoxazine ring endows benzoxazinorifamycins with unique physical and chemical characteristics which favor the use of rifalazil and derivatives in treating diseases caused by the obligate intracellular pathogens of the genus chlamydia. Minimal inhibitory concentrations of benzoxazinorifamycins against chlamydia are in the pg\/mL range. These compounds have potential as monotherapeutic agents to treat chlamydia\u2010associated disease because they retain activity against chlamydia strains resistant to currently approved rifamycins such as rifampin. A pivotal clinical trial with rifalazil has been initiated for the treatment of peripheral arterial disease. The rationale for this innovative use of rifalazil, including the association of<jats:italic> C. pneumoniae <\/jats:italic>in atherosclerotic plaque formation, as well as rifalazil's potency and efficacy against chlamydia in both preclinical and clinical studies, is discussed. Other benzoxazino derivatives may have utility as stand\u2010alone topical antibacterials or combination antibacterials to treat serious<jats:italic> Gram<\/jats:italic>\u2010positive infections. None of the benzoxaminorifamycins examined to date induce the cytochrome P450 3A4 enzyme. 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